Benzene, 1-isocyanato-2-methoxy- → HCID 71513650, compound

HRID 588751Notes

Reaction equation

HRID 588751 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:5]2[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[O:33]>ClCCl.C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][N:20]([C:32]([NH:31][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][CH3:23])=[O:33])[CH2:19][CH2:18]2)[C:5]2[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][S:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 117642418HCID 117642418, compound

Product 1

HCID 71513650HCID 71513650, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 10 (50 mg, 0.15 mmol) in dichloromethane (2 mL) and acetonitrile (1 mL) was added 2-methoxyphenyl isocyanate (21 μL, 0.16 mmol). The reaction mixture was stirred overnight. The reaction mixture was evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 0.5% to 3% methanol in dichloromethane), yielding the title compound (42 mg) as a white powder. MS (m/z) 462 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe crude residue was purified by silica gel flash chromatography
  3. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-8adc40a390404e829168908defe104de
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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